Day: September 28, 2021

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 38940-62-4, name is 3-Acetyl-5-bromopyridine. This compound has unique chemical properties. The synthetic route is as follows. Safety of 3-Acetyl-5-bromopyridine

A solution of 1-(5-bromopyridin-3-yl)ethanone (2.04 g, 27.5 mmol) in methanol (55 mL) was added slowly to a cold solution of 2-oxoacetic acid (2.04 g, 27.5 mmol) and potassium carbonate (7.22 g, 52.24 mmol) in water (50 mL). The mixture was stirred at room temperature for 2h. The resultant solution was partially evaporated under reduced pressure at 30 C to remove most of the methanol and then extracted three times with ethyl acetate. The cooled aqueous solution was carefully treated with acetic acid (11 mL, 192 mmol) and washed with dichloromethane. Ethylhydrazine oxalate (3.61 g, 26.1 mmol) was added to the aqueous phase, and the mixture heated under reflux for 2 h. A further 3.61 g ethylhydrazine oxalate (26.12mmols) was added and the mixture heated under reflux for 2 d. The solution was neutralised with potassium carbonate to pH 7 and was extracted three times with ethyl acetate. The combined organic layers were washed with brine, and dried over anhydrous sodium sulphate. The solvent was removed under reduced pressure and the crude purified in a 40M column from Biotage on a SP1 automatic purification system using hexane and ethyl acetate as solvents (0-100% ethyl acetate) in 20 column volumes. The appropriate fractions were collected and evaporated to give 3.71 g (47% yield) of the title compound. HPLC/MS (9 min) retention time 5.32 min. LRMS: m/z 282 (M+1)

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 38940-62-4, 3-Acetyl-5-bromopyridine.

Reference:
Patent; Almirall, S.A.; EP2196465; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 945557-04-0, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.945557-04-0, name is 5-Bromo-3-chloropicolinonitrile, molecular formula is C6H2BrClN2, molecular weight is 217.4505, as common compound, the synthetic route is as follows.

Acetyl 2,4,6-tri-O-acetyl-3 -azido-3 -deoxy- 1 -thio-cL-D-galactopyranoside (250 mg, 0.64 mmol) and 5-bromo-3-chloro-pyridine-2-carbonitrile (280 mg, 1.28 mmol) were dissolved in DMF (10 mL). Diethylamine (0.15 ml) was added. The reaction was stirred at room temperature with for 20 h. Water (50 mL) and DCM (50 mL) were added. The aqueous phase was extracted with DCM (50 mL X 2), the combined organic phases were washed with water (100 mL) and brine (100 mL), dried over anhydrous sodium sulphate. Removal of solvent gave a residue. The residue was purified by column chromatography (PE/EA=3/1) to obtain the product (130 mg, 38%).5-Chloro-6-cyano-3-pyridyl 2,4,6-tri-O-acetyl-3-azido-3-deoxy-1-thio-cL-D- galactopyranosidein/z calcd for [C18H18CLN5O7S] [M+H]: 484.0; found: 484.0.5-Bromo-2-cyano-3-pyridyl 2,4,6-tri-O-acetyl-3-azido-3-deoxy-1-thio-cL-D- galactopyranosidein/z calcd for [C18H18BrN5O7S] [M+H]: 528.0; found: 528.0. To a mixture of 5-Chloro-6-cyano-3-pyridyl 2,4,6-tri-O-acetyl-3-azido-3-deoxy-1- thio-cL-D-galactopyranoside and 5 -Bromo-2-cyano-3 -pyridyl 2,4,6-tri-O-acetyl-3 – azido-3-deoxy-1-thio-cL-D-galactopyranoside (130 mg) in CH3CN (5 mL) were added DIEA (0.23 mL), Copper(I)Iodide(15 mg, 0.08 mmol), CsF(82 mg, 0.54 mmol), 2-(4- chloro-3 ,5 -difluoro-phenyl)ethynyl-trimethyl-silane( 132 mg, 0.54 mmo 1). The reaction was stirred at room temperature for 20 h under a N2 atmosphere. Water (10 mL) and DCM (10 mL) were added. The aqueous phase was extracted with DCM (5 mL X 2), the combined organic phases were washed with water (20 mL) and brine (20 mL), dried over anhydrous sodium sulphate. Removal of solvent gave a residue. The residue was purified by column chromatography (PE/EA=2/1) to obtain the products 110 (80mg) and 111 (20mg).110) 5-Chloro-6-cyano-3-pyridyl 2,4,6-tri-O-acetyl-3-deoxy-3- [4-(4-chloro-3,5- difluorophenyl)- 1H- 1 ,2,3-triazol- l-ylj – 1-thio-a-D-galactopyranosidem/z calcd for [C26H21Cl2F2N5O7S] [M+H]: 656.0; found: 656.0.1H NMR (400 MHz, CDC13) oe 8.63 (d, J 1.9 Hz, 1H), 8.01 (d, J 2.0 Hz, 1H), 7.83 (s, 1H), 7.45 (t, J= 6.3 Hz, 2H), 6.34 (d, J 5.5 Hz, 1H), 6.16 (dd, J 11.7, 5.6 Hz, 1H), 5.63 (d,J= 2.3 Hz, 1H), 5.20 (dd,J= 11.7, 3.1 Hz, 1H), 4.78 -4.71 (m, 1H), 4.14 (tdd, J= 12.8, 8.7, 4.4 Hz, 3H), 2.08 (s, 3H), 2.00 (s, 3H), 1.98 (s, 3H).ill) 5-Bromo-2-cyano-3-pyridyl 2,4,6-tri-O-acetyl-3-deoxy-3- [4-(4-chloro-3,5- difluorophenyl)- 1H- 1 ,2,3-triazol- l-ylj – 1-thio-cL-D-galactopyranosidem/z calcd for [C26H2iBrCIF2N5O7S] [M+H]: 700.0; found: 700.0.

Statistics shows that 945557-04-0 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-3-chloropicolinonitrile.

Reference:
Patent; GALECTO BIOTECH AB; ZETTERBERG, Fredrik; NILSSON, Ulf; LEFFLER, Hakon; (105 pag.)WO2018/11094; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 779345-37-8, Adding some certain compound to certain chemical reactions, such as: 779345-37-8, name is 5-Fluoro-2-nitropyridine,molecular formula is C5H3FN2O2, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 779345-37-8.

Synthesis of compound 224.1. To a solution of 220.1 (0.300g, 2.1 lmmol, l .Oeq) in DMSO(5ml) was added 2-methylpropan-2-amine (0.185g, 2.533mmol, 1.2eq.) and DIPEA (2.72g, 21.1 lmmol, lO.Oeq.). The reaction mixture was heated at 100 C for lh. After completion of reaction, mixture was poured in water, quenched with NH4C1 solution and extracted with EtOAc. Organic layers were combined, dried over sodium sulphate and concentrated under reduced pressure to obtain crude which was purified by chromatography to get pure 224.1 (0.225g, 54.59%). MS(ES): m/z 195.22 [M+H]+.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 779345-37-8, 5-Fluoro-2-nitropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NIMBUS LAKSHMI, INC.; MASSE, Craig E.; GREENWOOD, Jeremy Robert; ROMERO, Donna L.; HARRIMAN, Geraldine C.; WESTER, Ronald T.; SHELLEY, Mee; KENNEDY-SMITH, Joshua Jahmil; DAHLGREN, Markus; WO2015/131080; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 2875-18-5, Adding some certain compound to certain chemical reactions, such as: 2875-18-5, name is 2,3,5,6-Tetrafluoropyridine,molecular formula is C5HF4N, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 2875-18-5.

General procedure: To a solution of fluoroarene (0.1 M) and HSiEt3 (0.1 M) in benzene-d6 in a PFA tube alpha,alpha,alpha-trifluorotoluene (1?2 muL) was added as internal standard. The PFA tube was closed by a Teflon plug, inserted into an NMR tube and an initial 19F{1H} NMR spectrum was recorded. Then [Rh(mu-H)(dippp)]2 (1) (0.005 M) was added and the reaction mixture was heated to 50 °C for 48 h. Hydrodefluorination of pentafluoropyridine gave 2,3,5,6-tetrafluoropyridine (11percent), 2,3,4,5-tetrafluoropyridine (11percent), 2,3,5-trifluoropyridine (8percent), 3,5-difluoropyridine (6percent) and 2-fluoropyridine (1percent) (TON = 11). Hydrodefluorination of 2,3,5,6-tetrafluoropyridine or 2,3,5,6-tetrafluoropyridine or 2,3,5,6-tetrafluoropyri-dine gave 2,3,5-trifluoropyridine (24percent), 2,3,6-trifluoropyridine (7percent), 3,5-difluoropyridine (15percent), 2,5-difluoropyridine (2percent) and 2-fluoropyridine (8percent) (TON = 18). Hydrodefluorination of hexafluoro-benzene or hexafluoroben-zene or hexa-fluorobenzene gave pentafluorobenzene (12percent) and 1,2,4,5-tetra-fluorobenzene or 1,2,4,5-tetrafluoro-benzene or 1,2,4,5-tetrafluoroben-zene (2percent) (TON = 3.1). Hydrodefluorination of pentafluorobenzene gave 1,2,4,5-tetrafluorobenzene (35percent), 1,2,3,4-tetrafluorobenzene (3percent), 1,2,4-trifluorobenzene (23percent) and 1,4-difluorobenzene (4percent) (TON = 19). Yields of organic hydrodefluorination products were determined from 19F{1H} NMR spectra by integration of product resonances versus the internal standard. Hydrodefluorination products were identified by NMR spectroscopy by comparison with literature data [23]. TON: number of hydrodefluorination steps/moles of 1.

According to the analysis of related databases, 2875-18-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Za?mostna?, Lada; Ahrens, Mike; Braun, Thomas; Journal of Fluorine Chemistry; vol. 155; (2013); p. 132 – 142;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.875781-17-2, name is 5-Bromo-1H-pyrazolo[3,4-b]pyridine, molecular formula is C6H4BrN3, molecular weight is 198.0201, as common compound, the synthetic route is as follows.name: 5-Bromo-1H-pyrazolo[3,4-b]pyridine

Step 4: Synthesis of 5-bromo-3-iodo-lH-pyrazolo[3,4-b]pyridine.[0220] 5-bromo-17J-pyrazolo[3,4-b]pyridine (3.00 g, 15.2 mmol) and A’-iodosuccinimide(3.60 g, 16.0 mmol) were dissolved in anhydrous dichloroethane (100 mL). The resultingmixture was stirred under reflux conditions for 6 h, cooled to room temperature and dilutedwith THF (300 mL). The resulting solution was washed with a saturated aqueous solutionof sodium thiosulfate (100 mL) and brine, then dried over magnesium sulfate, filtered andconcentrated. The residue was titurated with a 1:1 mixture of dichloromethane and etherand then ether before being dried in vacuum to afford 5-bromo-3-iodo-l//-pyrazolo[3,4-bjpyridine (3.795 g, 77% yield) as a beige-brown solid. ^-NMR (500 MHz, Patent; SGX PHARMACEUTICALS, INC.; WO2006/15124; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1594-58-7, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.1594-58-7, name is N-Hydroxynicotinimidamide, molecular formula is C6H7N3O, molecular weight is 137.14, as common compound, the synthetic route is as follows.

3-(3-(pyridin-3-yl)-1 ,2,4-oxadiazol-5-yl)benzonithle 3-Pyridylamideoxime (Aldrich, 5.5 g, 40 mmol) was dissolved in 60 mL of pyridine and 3-cyanobenzoyl chloride (Aldrich, 6.6 g, 40 mmol) was added. The reaction mixture was heated to reflux for 4 hours and then cooled to room temperature. The solution was poured into water (500 mL), filtered, and the solid were collected and dried under vacuum. ^ H NMR (300 MHz, methanol- d4) delta ppm 7.87 (td, J=8.0, 0.7 Hz, 1 H), 8.10 (dt, J=8.1 , 1.4 Hz, 1 H), 8.23 (ddd, J=8.1 , 5.6, 0.8 Hz, 1 H), 8.56 (ddd, J=8.0, 1.7, 1.2 Hz, 1 H), 8.64 (td, J=1 .7, 0.7 Hz, 1 H), 9.04 (dd, J=5.4, 1 .0 Hz, 1 H), 9.23 (dt, J=8.1 , 1 .7 Hz, 1 H), 9.57 (d, J=1.7 Hz, 1 H); MS (+ESI) m/z 249 (M+H)+.

Statistics shows that 1594-58-7 is playing an increasingly important role. we look forward to future research findings about N-Hydroxynicotinimidamide.

Reference:
Patent; ABBOTT LABORATORIES; WO2008/73942; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1086381-28-3, 4-Bromo-2-cyclopropylpyridine, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, 1086381-28-3, blongs to pyridine-derivatives compound. Quality Control of 4-Bromo-2-cyclopropylpyridine

Example 53i 1-(2-Bromopyridin-4-yl)-1-(2-cyclopropylpyridin-4-yl)-4-fluoro-1H-isoindol-3-amine Under an atmosphere of argon, tert-butyllithium (1.7 M in pentane) (0.576 mL, 0.98 mmol) was added dropwise to anhydrous tetrahydrofuran (4.00 mL) at -100 C. 4-Bromo-2-cyclopropylpyridine (0.097 g, 0.49 mmol) in anhydrous THF (2.00 mL) was added dropwise to the mixture. The solution was stirred for 2 minutes before dropwise addition of a solution of N-((2-bromopyridin-4-yl)(2-cyano-3-fluorophenyl)methylene)-2-methylpropane-2-sulfinamide (0.200 g, 0.49 mmol) in anhydrous THF (2.00 mL). The reaction was stirred at -100 C. for 20 minutes, then the temperature was raised to -78 C. over a period of 10 minutes. The reaction was stirred at -78 C. for another 60 minutes. MeOH (2.0 mL) was added dropwise at -78 C. followed by hydrogen chloride (1.25 M in methanol) (1.176 mL, 1.47 mmol). The cooling bath was removed and the reaction was left to stir at ambient temperature for 60 minutes. The solvents were evaporated and the residue was partitioned between EtOAc and saturated aqueous NaHCO3. The aqueous layer was extracted with EtOAc (*2), the organics were combined, dried (Na2SO4), filtered and evaporated. Purification by silica chromatography using 0 to 5% (3.5 M ammonia in methanol) in dichloromethane gave the title compound (0.094 g, 45%). 1H NMR (500 MHz, DMSO-d6) delta ppm 8.30 (dd, 2H) 7.72 (d, 1H) 7.58 (td, 1H) 7.42-7.47 (m, 1H) 7.37 (dd, 1H) 7.32 (dd, 1H) 7.18-7.22 (m, 1H) 7.00 (dd, 1H) 6.80 (br. s., 2H) 1.99-2.07 (m, 1H) 0.81-0.95 (m, 4H); MS (ES+) m/z 423, 425 [M+1]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1086381-28-3, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; US2010/125082; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 102368-13-8 ,Some common heterocyclic compound, 102368-13-8, molecular formula is C11H8N2O2S, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

A mixture of N-(3-amino-2,4-difluoro-benzyl)-2,2-dimethyl-propionamide (570 mg, 2.35 mmol), 1,1′-thiocarbonyldi-2(1H)-pyridone (550 mg, 2.35 mmol) and dioxane (20 mL) is stirred at reflux overnight. The reaction mixture is concentrated, diluted with DCM, filtered through a pad of silica gel and the filtrate is concentrated to give the title compound.Yield: 440 mg (65%). Rf=0.80 (silica gel, DCM:EtOH 95:5).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,102368-13-8, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2012/149676; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 131674-39-0, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 131674-39-0, name is 1-(2-Chloropyridin-3-yl)ethanol. A new synthetic method of this compound is introduced below.

Step 2: 1-(2-Chloropyridin-3-yl)ethanone A solution of 1-(2-chloropyridin-3-yl)ethanone (10 g, 0.0635 mol) in dry acetone (200 mL) was introduced under argon into a 1 L flask. The mixture was cooled to -30 C. and pure, pulverized chromic anhydride (19 g, 0.19 mol) was added. The reaction mixture was kept at room temperature for 3 h. 2-Propanol (100 mL) was added, followed by aqueous sodium hydrogen carbonate to pH 8. After filtration, solids were washed with chloroform. The organic and aqueous layers were then separated and the aqueous layer was extracted with chloroform (2*100 mL). The combined organics were dried over anhydrous sodium sulfate and evaporated to yield the crude pyridyl ketone as an oil. This product was purified by column chromatography (8 g, 81%). *1H NMR (CDCl3) 8.44 (dd, J=5 and 2 Hz, 1H) 7.91 (dd, J=7.5 and 2 Hz, 1H), 7.34 (dd, J=7.5 and 5 Hz, 1H), 2.68 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,131674-39-0, 1-(2-Chloropyridin-3-yl)ethanol, and friends who are interested can also refer to it.

Reference:
Patent; Georg, Gunda I.; Tash, Joseph S.; Chakrasali, Ramappa; Jakkaraj, Sudhakar Rao; US2006/47126; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 1001413-01-9, name is 1-(3,4-Difluorobenzyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C13H9F2NO3

The carboxylic derivative 3 (300 mg, 1.13 mmcl) and the amine 2(168 mg, 1.13 mmcl) were combined through a condensation reaction in presence of thecondensing agent TBTU (363 mg, 1.13 mmol). The solvents were evaporated under reduced pressure and the crude product was purified by flash chromatography over silica gel, using 0 – 4% MeOH as a gradient in CHCI3, to obtain pure SST143 as a white solid (210 mg, 0.53 mmol, 47% yield). mp: 285-288 00 1H-NMR (400 MHz, DMSO-d6): 6 3.48 (5, 2H, CH2 indole); 5.28(5, 2H, CH2); 6.68 (dd, 1 H, J= 6.8, 7.2 Hz, Ar); 6.77 (d, 1 H, J= 8.4 Hz, Ar); 7.20-7.23 (m, 1H, Ar); 7.40-7.52 (m, 3H, Ar); 7.66 (5, 1H, Ar); 8.29 (dd, 1H, J= 2.2,6.8 Hz, Ar); 8.46 (dd, 1H, J= 2.2, 6.8 Hz, Ar); 10.33 (5, 1H, NH), 11.87 (5, 1H,NH) ppm. 13C-NMR (101 MHz, DMSO-d6): 6 176.23, 161.54, 160.73, 150.35,147.90, 143.78, 143.42, 139.86, 134.02, 132.32, 126.40, 124.90, 120.35,119.02, 117.74, 117.25, 116.90, 109.10, 107.22, 51.45, 36.02 ppm. 19F-NMR (376 MHz; DMSO-d6): 6-138.17 (d, iF, J= 24 Hz); -139.76 (d, iF, J= 24 Hz) ppm. Anal. Calcd for 021H15F2N303: 0, 63.80%; H, 3.82%; N 10.63%; Found: C, 63.72%; H, 3.55%; N, 10.50%

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 1001413-01-9, 1-(3,4-Difluorobenzyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid.

Reference:
Patent; INTERNATIONAL SOCIETY FOR DRUG DEVELOPMENT S.R.L.; SESTITO, Simona; DANIELE, Simona; MARTINI, Claudia; RAPPOSELLI, Simona; PURICELLI, Guido; (63 pag.)WO2016/198597; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem